On terminal alkynylcarbinols and derivatization thereof

Dymytrii Listunov, Valérie Maraval, Nathalie Saffon-Merceron, Sonia Mallet-Ladeira, Zoia Voitenko, Yulian Volovenko, Yves Génisson, Remi Chauvin

Abstract


The chemistry of three prototypes of secondary alkynylcarbinols (ACs), recently highlighted as challenging targets in anti-tumoral medicinal chemistry, is further documented by results on n-alkyl, alkynyl and alkenyl representatives. The N-naphthyl carbamate of an n-butyl-AC is thus characterized by X-ray crystallography. A novel dialkynylcarbinol (DAC) with synthetic potential is described, namely the highly dissymmetrical triisopropylsilyl-protected version of diethynylmethanol. The latter is shown to act as a dipolarophile in a selective Huisgen reaction with benzyl azide under CuAAC click conditions, giving an alkenyl-AC, where the alkene unsaturation is embedded in a 1,4-disubstituted 1,2,3-triazole ring, as confirmed by X-ray crystallography.

Supplementary information (CIF file)

Keywords


alkyne; alkynylcarbinol; pharmacophore; design; propargylic alcohol; 1,2,3-triazolylcarbinol

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References


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DOI: https://doi.org/10.17721/fujcV3I1P21-28

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